


Have You Ever Wanted to Try?

by Eugara



Category: Supernatural
Genre: Established Relationship, Handcuffs, Hey You Got Schmoop in My Porn, Humor, M/M, PWP, Prostitution Roleplay, Sexual Roleplay, Switching, Teacher/Student Roleplay, Truth Spells, Virginity Kink, etc. - Freeform
Language: English
Status: Completed
Published: 2015-05-22
Updated: 2015-05-22
Packaged: 2018-03-31 17:17:28
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 12,056
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3986335
Author URL: https://archiveofourown.org/users/Eugara/pseuds/Eugara
Summary: <blockquote class="userstuff">
              <p>Season 8.  There's nothing wrong with a little make-believe...</p>
            </blockquote>





	Have You Ever Wanted to Try?

“Y’know, I gotta say,” Dean drawls, jerking his wrists against the handcuffs restraining him to the cheap wood of the motel chair, “I’m actually a tad impressed.” He subtly tests his bonds again and the cuffs give a little clink at the motion. They’re the real deal. No way to pick the lock with his hands empty like they are. “This is the first time one of you boys actually managed to get the drop on me. Think you’ll manage to swing a promotion out of the deal?”

The federal agent leaning against the edge of the room’s table doesn’t budge an inch, arms crossed over his chest and his long legs stretching out in front of him for miles. The perfect picture of casual indifference. Like he can wait Dean out forever. “Maybe I’m just in it for the thrill of capturing the infamous Dean Winchester,” he says, raising a lone eyebrow. The rest of his face remains as blank as stone.

Dean thinks the statement over for a while before he makes a face. “Nah. Traditional guy like you?” He tosses the suit his most cutting smirk. “I bet you’re all sorts of ‘by the book’. Probably organize your socks by color.” The guy’s eye twitches at that one and Dean knows he’s hit a home run. It’s the only reaction the other man gives though. “Speaking of thrills,” Dean says, aiming for offhand. “Hand on the Bible. This whole Bureau thing exciting enough for you?” He glances up at the man from under his eyelashes, oozing sarcasm through his teeth. “It all you ever dreamed?”

The agent holds his steady gaze, like he’s carefully measuring his breaths before answering. Dean wonders if HQ would have trained him for this particular situation. Wonders what the Field Office would have said in order to warn him about Dean Winchester. _Silver fucking tongue on that one, so you shouldn’t let him run his mouth. And dear god, make sure you don’t let him talk you into anything._ “The work I do is important,” the guy eventually replies, tone intentionally even. “I get to stop criminals like you.”

“You didn’t answer the question,” Dean says lowly, a slow grin creeping over his features. He deliberately spreads his legs, then catches the fed’s eyes flicking down to his crotch for half a second before guiltily jerking back up to meet his face. Dean can feel the instant heat pool down south at the obvious interest himself.  _Yahtzee_. “I’m exciting,” he purrs, throwing on his best _trust me_ expression.

“You’re a dangerous criminal,” the guy says, voice suddenly rough in the intimate space of the small room. His Adam’s apple bobs as he swallows hard. “There’s a difference.”

Dean spreads his knees a little further, until he’s completely open and on display with his arms wrenched back behind him the way they are. “ _Is_ there?” he counters suggestively.

The agent remains still for another minute before gracefully pushing himself to his feet, the only show of movement since he first strapped Dean down. His suit jacket seems to fit for the most part, but the shirt underneath is at least one size too small and it stretches pornographically across the breadth of his chest and shoulders every time he moves. And my, what impressive shoulders they are. A gorgeous specimen like him is fucking _wasted_ on the FBI. “And what, exactly,” he asks, “makes you think that I’m interested in any _excitement_ you have to offer?” The guy paces in front of him like a jungle cat, taking Dean in, studying every hair on his head, every twitch of his jaw. His muscles bunch under his ill-fitting suit with each step and Dean wants to strip him out of it. Get his hands on all that tan, mouth-watering skin that the layers of stiff fabric are trying to hide.

“You want it,” Dean says with a violently self-assured grin. “Your tie is loose.”

The other man comes to a halt, a slight smirk gracing his lips at the pointed observation. “Maybe I got dressed in the dark this morning. Or maybe I forgot to fix it after lunch.” He takes a step toward Dean, then intentionally leans over where he’s seated, bracing himself on the chair’s arms. “Who says it’s for you?”

Dean lets out a frustrated sound, straining forward to catch any skin he can, but the stubborn ass remains infuriatingly out of reach. “You know what your neck does to me,” he growls.

“And how would I know anything about you at all?” the agent asks insufferably. “We’ve only just met.” He grins again, and it highlights the striking cut of his perfect fucking dimples.

Dean swoons a little at the sight—he can’t help it—but this whole tables-being-turned thing is starting to make him feel just the slightest bit pissed off. So he decides to fight back with a little firepower of his own. He very intentionally and very slowly sneaks his tongue out to trace the contours of his lips, internally crowing when the other man sucks in a hitched breath. “C’mon, sweetheart,” Dean says temptingly. “You know you want a piece of this. Best ride of your life.”

“ _Agent_ ,” the fed corrects him.

Dean snorts at the curt reply. “Aw, what’s a matter, baby? You think I don’t respect you?”

Agent Hot-Ass wraps a hand around the chain of Dean’s cuffs and _yanks_ , slamming him against the back of his chair. “You call me ‘Agent’ or I leave you to rot in this shitty motel room until my colleagues come to pick you up.” Then he leans back over Dean again, warm breath curling around the shell of his ear. “And they aren’t as nice as I am.”

“Yeah, I’ll bet,” Dean breathes back. He struggles against his restraints one more time, almost letting out a whimper at the distance the other man is insistent on leaving between them. So painfully close, but not _quite_ near enough for Dean to actually reach anything. “Alright, G-man, you got me,” he admits, antsy from the incessant need gnawing at his nerves. “I’ll call you anything you want.” Dean hits the guy with his best bedroom stare, then tips his chin up until he’s close enough to whisper—his voice a wicked promise of what he can offer. “So how’s about you let me outta these cuffs and I show you a real good time?”

The agent swallows again as he mulls the offer over. “Actually,” he says eventually, “think I’ve got a better idea.” He casually pulls the handcuff keys from his jacket pocket and frees one of Dean’s wrists, slipping the chain from where it’s wrapped through the back of the chair. But before Dean can even blink, the goddamn _giant_ is suddenly wrenching his arm up behind him and snapping the cuffs back in place with a final click. He’s somehow managed to get Dean all trussed up again without him even realizing it—his hands firmly locked together at the small of his back. “Wouldn’t want you getting free now,” the guy murmurs playfully. Like he’s thought of fucking everything. “After all, we can’t have a dangerous criminal on the loose.”

Dean jerks against the other man’s grip to no avail, his chains clinking mockingly at the attempt to free himself. “This wasn’t the deal,” he growls.

“We didn’t have a deal,” the suit reminds him. “You just promised me the ride of my life.” He smiles at him like his own personal sin and salvation, all rolled up into one. “Didn’t say a thing about me letting you go in order to do it.”

Dean can’t help but feel the slightest bit impressed by the clever turnabout. But he’s _Dean fucking Winchester_. No way in _hell_ is one of Uncle Sam’s hatchet men gonna pull one over on him. So, he’ll have to play this a different way. Fine. No skin off his nose. Dean immediately lets his arms go slack in the fed’s hold, stepping closer into the warmth radiating from the man’s body and pressing up against the firm wall of muscle as he does his best impression of a cat in heat. “C’mon, baby,” he coaxes.

“ _Agent_.”

Dean ignores the correction. “You _that_ kind of guy? Just one and done?” He lets his breath whisper over the sliver of available skin at the base of the guy’s neck, grinning as he ineffectively tries to repress his automatic reaction to the warmer air. Or maybe it’s just his reaction to the sinuous press of Dean’s body against his own. “What are you gonna do when I’m all locked up and out of reach and you’re craving more?”

The agent stiffens at the insinuation, hands clenching and unclenching against Dean’s lower back, fingers still loosely wrapped around the chain of his cuffs. “You seem to think pretty highly of yourself.”

“Ain’t bragging if it’s the truth,” Dean says with a rakish smile. “I’m serious, _Agent_. Must have a pretty empty social life, the way you live. So what’re you gonna do afterwards, when you’re all by your lonesome in that too-cold, too-empty bed of yours…and you’re thinking about me?” He grazes his lips against the blade of his jaw—barely a feather touch—and the agent shivers.

“So, what?” the guy rasps, obviously trying to keep himself in check. “You think I’m just gonna let you go?” He lets out an overdramatic huff of breath. “Or better yet, come _with_ you? Like we’re Bonnie and Clyde or something?”

“The Alabama to my Clarence,” Dean appends. “You and me, darlin’. Four wheels and the open road. All you gotta do is say _yes_.”

The suit blushes brightly and ducks his head, letting the ends of his no-way-in-hell-is-that-regulation haircut sweep against Dean’s cheekbones. “I don’t think I can trust you,” he says, voice rough and strained tight with the wanting. They’re both hard by now—have been for a while—and Dean can feel the impressive length of the other man’s cock, burning hot and needy right through the fabric of his slacks. Urgent and unmistakable where it’s pressed up against the bone of his hip.

“I’m not asking you to trust me,” Dean whispers back lowly, teasing the tip of his tongue along the agent’s lower lip—reveling in each shuddering intake of breath. “…I’m asking you to fuck me.”

There’s a moment of absolute stillness. And then he’s suddenly being _pounced_ on with a vicious snarl, the man tackling them both to the bed like Dean’s words have snapped his leash. He wrenches his fingers hard down Dean’s sides before he’s flipping him over and shoving his face down into the starched comforter, one strong hand keeping him pinned as he savagely unhooks his belt and yanks his jeans below his ass. “God, I’m gonna fuck you so hard,” the agent growls. “Gonna pound that ass until you can’t fucking walk.”

“Promises, promises,” Dean manages to grit out from where his head is awkwardly bent against the coverlet, and then he’s rewarded with two fingers being abruptly shoved up inside him. Pressing and curling with no regard for mercy. Dean grunts at the unexpected sensation—a tight, strangled sound—and jams his face further into the bedspread, unable to stop his hips from unconsciously canting up for more.

“Yeah, that’s right,” the guy chuckles warmly. “Big, scary _Dean Winchester_. The stuff of nightmares. Already fucking _aching_ for it.”

Dean laughs into the bed underneath him, the cheap fabric heating up against his face with each puff of breath he lets out. “ _Someone’s_ aching for it all right,” he mumbles around a mouthful of polyester. “Unless that’s a Glock in your pocket.”

The agent slowly leans down to hover above his right ear, hair falling against Dean like a curtain of silk, tickling at the back of his neck as he speaks. “You’re a mouthy fucker, you know that?”

Dean twists back to catch him with a knife-edged grin, a wicked gleam in his eye. “Sure. Maybe we can try that next time.”

There’s a harsh zipping sound, and then Dean’s face is being shoved back down as the suit suddenly rams his _gigantic_ fucking dick into him without a single warning—practically splitting him in two. It shuts him up so fast that he can actually hear his teeth click as they violently snap together.

“ _God_ , yes,” the guy lets out in a strangled groan, fingers digging brutally into Dean’s hips as he immediately starts fucking him with short, choppy thrusts. His breath is coming out in heavy pants above him, and then his huge, calloused hands slide up and over Dean’s back, kneading at his shoulder blades through his t-shirt as the man’s hips keep pumping. “Feels so fucking good. You don’t even know.”

“ _Wanna_ know,” Dean growls seductively, arching his spine as best he can without the use of his arms, until the fed is practically whimpering due to the deeper angle. “ _Yeah_ ,” he gasps out. “C’mon, sweetheart. Want you to tell me.” And then Dean is suddenly hissing in pain as the guy violently yanks at the chain of his handcuffs. “Agen—Agent!” he shouts. “Fuck. I meant _Agent_.” His good behavior is quickly rewarded with a broad palm wrapped around his own straining cock, and Dean moans into the comforter at the sensation. “C’mon, _Agent_ ,” he says, his hips helplessly hitching forward into the man’s fist. “You’ve already got me right where you want me. So why don’t you _talk_ to me about it?”

There’s another few, sharp thrusts, and then the guy completely drapes himself over Dean, mouthing at the nape of his neck as he starts mumbling into his hairline. “Feel so fucking perfect,” he says, leaving little, sloppy-wet kisses along every bit of skin he can reach. “So _tight_. So good.” He nips at Dean’s jaw, teeth scraping against his stubble with a gentle rasping sound. “Don’t even know what you do to me. You have no fucking clue.” The agent twists his free hand up in the handcuff chain again and tugs. Not forceful enough to hurt this time—just a reminder. “And you’re _mine_ ,” he whispers ferociously, the edges of his voice quickly pitching up into a higher whine the closer he gets to the breaking point. “Can’t do anything at all.” His hips pick up speed, the rhythm stuttering into something clumsy and frantic. “You’re all tied up and pinned down and you’re **_mine_**.”

The agent suddenly jerks as he comes with a desperate whimper, his cock pulsing wetly until Dean can feel the guy’s spunk start to overflow and leak out around the rim of where his ass is stuffed full of federal cock. But his passionate words are still knocking around the inside of Dean’s skull, unbearable flames of lust searing at the edges of his limited self-control as he writhes against his bonds. He lets out a plaintive, strangled sound of his own before the man finally takes pity on him, wrenching Dean’s hips up and jacking him to completion until he’s following him right over the edge, spilling hot over long, nimble fingers.

Dean takes a long, deep breath—face still firmly planted against the scratchy bedspread for a few exhausted seconds—and then he bucks up a couple times until his brother finally gets the hint and drags his heavy ass off of him, pulling out with a lingering groan and the slick sound of too much lube. “Told you,” Dean mumbles into the mattress, too wrung-out to do much more than lay there and listen to Sam thump down beside him.

“I said yes, didn’t I?” Sam grumbles, still breathing heavily. Dean can easily imagine the eye roll that’s probably accompanying his brother’s words, but he sounds too pleasantly fucked-out for it to be anything but playful.

He smiles, then bends his elbows until he’s able to bump one into Sam’s arm. “You should listen to me more often. I’m a genius.”

There’s a snorting sound from the head of the bed, but Sam chooses not to break their little bubble of post-orgasmic euphoria with a well-placed insult. And Dean’s actually pretty grateful for the reprieve. It would be undeniably more difficult—but not impossible, _never_ impossible—to kick his brother’s ass with his arms still cuffed behind his back.

“Christ, dude,” Sam eventually gripes after a moment of silence. “I am never wearing your shirt again.” Dean can feel him wriggling around on his back as he tries to peel the strangling fabric off of his arms. “My _armpits_ are numb. I didn’t even know that was a thing that could happen.”

“Yeah, yeah. Bitch on your own time, princess.” Dean tries to manage some sort of attempt at standing, but can’t get a foothold with the way his jeans and boxers are currently tangled around his calves. “Sammy, c’mon,” he says gruffly. “Cuffs off.  _Now_.”

But Sam just huffs out a laugh and sprawls himself over Dean’s back, all bratty little brother now that he’s managed to strip most of his fed layers off. The clammy warmth of his chest is making Dean’s bare skin start to sweat where his t-shirt has ridden up and shifting around in irritation isn’t doing much at all to free him of his annoying new parasite. “I like you like this,” Sam mumbles into his hair, voice teasing and bright as he fiddles with Dean’s handcuffs. Then he goes completely still and lets out a thoughtful sound. “We should prep more often.”

Dean rolls his eyes at the impractical statement. Taking the time-out to slowly prepare either one of them in advance is a little too inconvenient for their usual spur-of-the-moment romps, but it’s definitely not without certain benefits. Like the fact that Sam carefully working him open a few minutes beforehand meant they were both revved up and ready to go practically from woof. Foreplay is dandy and all—and Dean has spent plenty an evening slowly winding his brother up until Sam can barely _breathe_ without crying from the sheer frustration—but it turns out that gunning from one hundred, right at the start, is actually pretty fucking great too.

Sam nips at the base of his neck, bringing him back to the present with a dangerous chuckle that doesn’t bode well for Dean at all. Especially not with his bare ass still hanging in the wind. “What’ll you give me if I let you out of the handcuffs?” his brother asks devilishly.

Dean just lets out an annoyed groan.

 

~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~

  

It all started as a joke.

Dean had half-heartedly brought up roleplaying as a way to spice up their bedroom antics after the whole Prometheus thing. Something about the titan spending all those years thinking he was someone else and _“Hey, bet you ten bucks that made things pretty crazy in the sack. Sure didn’t seem like his baby mama was complaining.”_  Dean didn’t even mean it, really. He’d just expected Sam to throw him one of his ever-popular bitchfaces and that would be that. It’s not like their fucking actually needs any more excitement—chasing down monsters and dodging death on a weekly basis tends to provide _plenty_ of fuel for adrenaline-spiked sexcapades—but instead, his brother had given him one of those ridiculously sappy looks of his and immediately agreed, conceding to Dean’s wishes without even a single complaint at all. Just solemn eyes and a grave nod. 

Knowing Sam, it was probably meant as an attempt to finish smoothing over the last few months of tension and bickering between the two of them. The bitterness over the whole Purgatory thing. Or over Amelia and Benny. It doesn’t really matter anyway because Dean had already let it go weeks ago. _Well_ …maybe not so much ‘let it go’ as ‘buried it deep, pretended it never happened, and then stubbornly refused to ever think about it again’. Alright, so Dean ain’t exactly a saint. What the fuck ever. He’d come to terms with that years ago.

Hell, maybe Sam giving into Dean’s stupid bedroom fantasies was just his version of a housewarming present, since they somehow managed to stumble across the fucking _El Dorado_ of magical bunkers and his brother hadn’t so much as tossed a fern his way. Dean gave Sam a pretty epic blowjob for _his_ housewarming gift. Although, now that he thinks about it, he’d never actually stated it as such, so it’s entirely possible that Sam just thought it was a regular blowjob. Maybe Dean can make him a lasagna or something now that they have an actual kitchen. Sam liked macaroni as a kid, and that’s pasta. Sort of. It’s basically the same thing.

Well, whatever the case may be—Dean has never been one to turn down a free pass for unimpeded lechery. Which is how they’ve managed to find themselves, barely a week later, behind the closed doors of a Drake University lecture hall. _Way_ after hours. 

Sam is pretending to grade schoolwork down at the front of the room, loose sheets of paper spread out over the low, flat table in front of him as he flits over each one with seemingly unerring focus. Dean takes an idle moment to wonder if some absent-minded professor type is gonna come back on Monday to find his shit all out of order or if his brother just happened to yank a few blank pages out of the nearest printer. A subtle throat-clearing from the front of the room spurs Dean out of his thoughts and into motion. 

He shifts his shoulders to adjust the ‘Drake Bulldogs’ hoodie they’d managed to swipe from the campus bookstore, then makes his way down the hall’s steps, casually letting his fingers trail over the edge of each desk he passes by.  Sam is still intentionally all caught up in the game, pretending to ignore Dean in favor of the papers he’s fussing over. He scoops a few up, tapping their edges against his desk to even out the corners, and then eventually graces Dean with a brief moment of eye contact. “You are aware that my office hours are Monday through Thursday, right?” he says off-handedly, attention still clearly on his fake work. He sweeps his hands over the pile of paper, gracefully smoothing out the edges, then lets his long fingers rest on top of the stack. “I’d be happy to help you then.”

Dean cocks a hip against the guardrail beside him and slips his hands into the hoodie’s front pocket, doing his best to emanate nothing but pure sincerity. “But see, I’ve really got a problem here, _Professor_.” He pins Sam with his most trustworthy grin. “It’s about, uh…school stuff,” he says. “Homework.”

His brother raises an eyebrow. “You mean the essays?”

“Uh, sure. Yeah.” Dean’s not really sure that _accuracy_ needs to be a part of whatever game they’re in the middle of here, but Sam’s running the show this time, so he keeps his grievances to himself and plays along as best he can. He takes a step forward, then leans in over his brother’s desk, ducking his head to catch Sam’s gaze with a yearning one of his own. “I have a major problem with my essay,” he says, obediently following Sam’s nudging. “Real urgent. Can’t wait ‘til Monday.”

“Is that so?” Sam taps his fingers over the papers one more time, and then finally gives Dean his full attention. He slips the pair of borrowed reading glasses from the bridge of his nose and collapses them inwards, gently placing them at the corner of the low table—and Dean feels a slight twinge of regret at the motion. They actually didn’t look half bad on his brother. “Which one of my classes are you in?” Sam asks coolly, shaking him from his musings.

He rolls his eyes at the unnecessary questioning. Leave it to Sam to worry about all the irrelevant details during _roleplaying_. “The, uh—the _big_ one.”

Sam hums distractedly, small smile twitching at the corners of his mouth. “I can’t place your face,” he says with a teasing glint in his eye. “And you are quite a bit older than the rest of my students.”

Dean instantly bristles at the implied insult, keeping his jaw clamped shut before it can spit out something equally goading in return. “Never too old to learn, right?” he grits through his teeth.

“You know,” Sam drawls, relaxing back in his chair and lacing his fingers over his abdomen, “I think I _do_ remember your essay. Dean, right?” He runs his tongue over his teeth, shaking his head disappointedly before he opens his mouth again with a sharp sucking sound. “I wasn’t very impressed, Dean. Seems like you were off screwing around instead of doing the proper research for your report.” Sam plucks a stray thread from the tan fabric of his sweater vest, then slides a hand over his chest to sweep it away. They’d bought the thing for that Thule case a little under a month ago, when Sam had to pass for a research assistant, but Dean’s never been happier to find a different (and better) use for one of their undercover duds. “So if you’re here to get me to change your grade,” his brother continues sternly, “I’m afraid I can’t help you.” Then he lets a slow smile crawl across his face, leaning forward until Dean can make out every single fleck in his hazel eyes. “You see, I’m not the type to typically be _persuaded_.”

Dean lets a shameless grin of his own curve over his lips at the opening, slowly making his way around the desk. “Well, Professor,” he starts lowly, soaking his voice in sex. “What if I was to tell you that I was majoring in _persuasion?”_

Sam leans back in his chair as he rounds the table, his slim thighs spreading just the slightest bit as Dean comes to a stop directly in front of him. “You think you’re up to the task?” he asks throatily.

Dean sinks down to his knees in one smooth motion, never breaking eye contact until he’s fully kneeling between his brother’s legs. “How about you tell me?” he whispers. Dean gently wraps his hands around Sam’s calves, leisurely trailing his fingertips up behind the backs of his knees until he can get a good enough grip to _yank_ him forward with one sudden pull. Sam lets out a little, hitched noise at the movement, and then relaxes into his touch, trusting and eager. His hands are white-knuckling the armrests of his rolling chair, but everything below the waist is pliable and tilting toward every single one of Dean’s movements. He rewards the enthusiasm by grazing his lips up the inner seam of his brother’s slacks, letting his hot breath creep over the very noticeable bulge straining against the fly.

“We shouldn’t be doing this,” Sam breathes, his legs trembling with anticipation. Or maybe just trembling at the thought of them being caught.

Dean grins and massages a hand over the outline of Sam’s cock, pressing down until his brother tosses his head back with a sinful moan. “But that’s what makes it fun,” he whispers. Dean slinks forward to shove his face into Sam’s lap, powering through the delicious litany of gasps and whimpers as he latches onto the zipper with his teeth. He slowly drags the tab down, relishing in each quiet click of interlocking metal, until Sam’s erection springs free with another heated moan. “No underwear, Professor?” Dean teases. “How naughty. I’m shocked.”

“You’re losing points for talking,” Sam says tersely, and Dean immediately shuts the fuck up in favor of laving his tongue over the crown of the weeping cock in front of him.

He ducks down to lick a broad stripe up the underside, and then draws back to circle around the tip, the bitter salt of his brother’s pre-come bursting over his taste buds. He’s supposed to be the one riling Sam up here, but just a taste gets his own dick twitching against the inside of his jeans. Dean purses his lips up against the slit, and then slowly opens them, pushing forward and swallowing as much as he can. Sam makes a wrecked noise above him, and Dean has to fight back a grin in order to avoid catching his brother with his teeth.

“ _God_ , Dean,” Sam hisses, writhing against the back of his chair as he strains to keep still. “God, your fucking _mouth_.”

Dean glances up through his eyelashes, deliberately adding to the effect, and then chuckles as Sam groans again. And apparently, the punctuated vibrations are setting him off too because Sam just whines plaintively and hitches his hips up at Dean’s quiet laughter. He’s a gorgeous mess like this, wet cock jutting out from the rest of his neat and tidy prep wear. The immaculate blazer and sweater set a perfect juxtaposition to the smears of pre-come and saliva Dean’s leaving against the material of his fly.  _Fuck_ , he looks good. In fact, he looks almost perfect.

Dean pulls back to fumble his hand out over the desk beside them, ignoring Sam’s whimper of protest as he blindly searches for his prize. His fingers finally hit plastic and he lets out a silent cheer, falling back against Sam with the frames of Professor Whoever’s reading glasses clutched in one triumphant hand. Luckily, his brother seems to catch his drift without too much fuss, and he’s instantly ducking his head down for better access, endlessly patient as he lets Dean carefully slip the specs back over his nose.

“ _God_ , there you go,” Dean whispers, the glasses succeeding in making Sam look like even more of a beautiful disaster. His hair is in complete disarray, little tendrils sticking to the sweat on his forehead and catching on his lower lip, and his cheeks are completely flushed with want. He looks like a goddamn walking wet dream. And even though Dean knows this whole ‘Hot for Teacher’ shit is all _Sam’s_ fantasy, he can’t help but wonder if he’s riding a kink of his own here.

Dean slowly brings his hand up to his mouth, keeping his eyes locked on Sam’s as he deliberately drags his tongue flat against the skin, wetting his palm so he can curl it around the base of Sam’s erection and _pull_. Pumping his hand up and letting his mouth descend over the rest of the heated length again until his lips meet his knuckles.

Sam lets out a breathy growl at the motion, gripping the sides of Dean’s head hard and shoving up into his throat as far as he’ll let him. “You’re being so good for me,” he pants. “So goddamn good.” His legs wobble dangerously as he tries to scoot closer, and Dean wraps his free hand around his thigh to steady him. “So fucking deep,” Sam’s purring again. Or attempting to, at least—it’s mostly consonants at this point. His brain tends to shut off whenever he gets this close to the edge. Actually, it’s one of Dean’s very favorite things about sex with Sam. Working his genius little brother up to the point where he completely forgets how to speak English is one of the biggest ego-trips Dean gets to experience on a regular basis. He stiffens his tongue, then rubs it in little circles against the underside of his brother's crown, bringing his wet hand down to fondle the weight of Sam’s balls. It only takes a few, firm rolls of his palm to finally get Sam’s fingers wildly scrabbling at the back of Dean’s head, yanking him forward with absolutely no regard for his need to breathe as his dick pulses messily down his throat.

Sam keeps him there until he’s completely spent, hands weakly petting over the sides of his face, and Dean can’t even work up the words to complain while his brother is still lying warm and heavy on his tongue. He slowly pulls away, chuckling at the weak noise of protest from above, until he can fully take in the sight of Sam slumped against the back of his chair.      

His brother looks thoroughly _wrecked_. In the most delicious way. His glasses are completely askew, and sweat is tingeing the collar of his dress shirt wherever it brushes up against his glistening throat, and his eyes keep trying to slip shut over his happily sated expression.

“So,” Dean drawls, slipping his brother’s spent cock back into his pants and helpfully zipping him up. “How was that, Professor?”

Sam just blinks at him for a second until he manages to gather up enough energy to drag the cockeyed frames from his temples and carelessly toss them back onto the desk with a click of plastic. Then he gives Dean a look so heated that it’s worthy of an actual demon. A sexy demon. Like an incubus or something. “Well, I’d say you definitely earned a rewrite on that essay,” he says, fighting back a half-lidded smile.

“A _rewrite?”_ Dean repeats, completely floored. “Are you fucking kidding me? That blowjob was worth an A-plus. At _least_.”

Sam giggles—like an actual, full-fledged _giggle_ —his voice reedy with amusement. “What kind of professor do you take me for?” he asks teasingly, wrapping his legs around Dean’s waist so that he can yank him in closer. “I would never undermine the sanctity of academic integrity by giving out an undeserved grade.”

“Undeserved, my ass,” Dean says with a bitterness he doesn’t really feel. There’s no use trying to escape his brother’s octopus limbs, especially when he’s in a good mood like this, so Dean steers into the weird embrace. “In fact,” he says, running his hands up Sam’s thighs, and subtly wiping the remaining spit onto his brother’s slacks, “you should probably just give me credit for the next three papers as well. If we’re being fair and all.” He lets his palms come to a stop, resting warm against the wings of his brother’s hips, and then forces out a playful scoff. “Talking about _deserved_.”

Sam grins and leans in for a relatively chaste kiss. “Maybe you can _really_ convince me if—” He pulls back with a sudden jerk, the humor instantly vanishing from his face as he descends into an unexpected coughing fit.

“Shit, Sammy. You okay?” Dean manages to untangle himself as quickly as he can, reaching up to rub his dry hand over the splay of Sam’s upper back. “What, you accidentally swallow a fly or something?” he jokes lightly. But his brother ignores him as his shoulders convulse under the worrisome hacking. There’s a box of tissues on the professor’s desk, and Sam flounders a hand around in their general direction until Dean finally gets the message and snatches up a handful to pass his way. “Seriously, dude,” he says, frowning as the coughing slowly subsides. “You okay?”

“Yeah, I’m fine,” Sam eventually croaks. Sounding for all the world like he’s anything but. He thoroughly wipes at his mouth with the tissues, and then immediately crumples them into a tight ball and shoves his hand under the desk. Completely hidden from view. “Must have been dust or something,” he says weakly.

Dean raises a skeptical eyebrow. The lecture hall is newer and shinier than every room they’ve ever slept in combined. “What dust?”

Sam just gives him a flippant shrug before scooting his chair out and chucking his tissue wad into the nearest wastebasket. “We should go, don’t you think?” he says quickly, rubbing his palms over his dark slacks. “Get out of here before some night janitor finds us.” He flaps an indicative hand in the general direction of Dean’s crotch. “I’ll make sure and get you back once we’re in the motel room.”

Dean blinks at his brother’s suspicious jumpiness, blindsided by the sudden whirlwind of motion. “I don’t think we’re in any danger here, man,” he says, jerking a thumb at the darkness of the hallway outside. “Groundskeeper Willie ain’t showing up ‘til Monday.”

But Sam blatantly ignores any of Dean’s logic, turning his face into his elbow as he clears his throat against another round of coughing. “C’mon, Dean. You know how you get.” He attempts a convincing smile. “I wouldn’t want Professor Stanton to have to explain why there’s come stains all over—” he pauses to glance down at the desk, “…Brenda Mahari’s essay on the African diaspora.”

“You swallow the way you’re supposed to, there won’t be any come stains to explain away in the first place,” Dean grumbles quietly. But he doesn’t really mean it. Priority number one is getting his brother somewhere safe and comfortable before he hacks up a lung. Maybe there is some sort of hyper-sensitive dust in here. Or maybe Sam’s just allergic to reciprocating. Dean slips the Drake hoodie from his shoulders and carelessly tosses it onto the professor’s desk. Then he makes his way around the table and jogs up a few steps until he can snatch his actual coat from where he’d flung it over one of the lecture chairs earlier. “Y’know,” Dean says persuasively, trying to press his luck, “he’d probably just give her an A out of guilt. Might be worth it to stay and help a girl out.”

His brother makes a cagey noise in response, wiggling his hand. “Honestly, it deserves a B-minus at best. She tends to stick to a more Western viewpoint. It’s a little reductive.”

Dean freezes in the middle of putting his jacket on, one of his arms still awkwardly caught up in the sleeve. “You actually read it?” he asks flatly. “We’re supposed to be playing ‘Don’t Stand So Close to Me’ here, and you took the time to read a freaking _essay?”_

“I just skimmed it,” Sam mumbles under his breath, cheeks burning with muted embarrassment as he lies through his teeth.  _Badly_. “A little.”

  

~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~

 

Dean stands with his back against the motel door, tapping his fingertips against the dented metal behind him and wondering if maybe they aren’t going a little too far this time. Sure, he’d played it off like a cheap porny fantasy when he first brought it up.  _“Virgins are sexy, Sammy. I mean, real ones are frigid, but pretend ones are hot. It’s like I’m corrupting your innocence, teaching you how to be **bad**.”_  He’d even made sure to add an inappropriate eyebrow waggle to underscore the ridiculous nature of his words. But for all of his posturing, that wasn’t the real reason why Dean wanted to do this. And he’d be an idiot to think that Sam and his giant brain hadn’t immediately picked up on his actual intentions.

 _“I want you to ask me.”_  That’s what he’d said. The first chink in a long line of truths that have the ability to send his armor tumbling down to his feet around him with just the slightest tap. The little voice that lives in the back of Dean’s head is _screaming_ at him to play this off. To go at this with every bit of cheesy, over-the-top dialogue he’s got crammed into his brain from years of trashy porn. But his little brother is awkwardly seated in the middle of one of the room’s double beds, his t-shirt off and balled against his chest as he picks at the material with nervous fingers. Sam’s a decent enough actor when he’s comfortable with it, and he looks perfect in this moment. Young, somehow. Fragile. Dean couldn’t walk away from this if he tried. He just ain’t that strong.

It isn’t even his fault anyhow. Dean’s usually much better about drowning his woulda-couldas in whiskey whenever they happen to rear their annoying heads. It’s just that the whole deal with Amelia had rubbed him raw. Scrounged around in his attic for a shit-ton of old insecurities and brushed off the dust. And hey, if Sam is willing to play ball, there’s no reason for Dean to let the opportunity go to waste.

“Say it again,” he commands quietly, pushing himself away from the door to take a few steps into the center of the room. Needing to hear it like it’s real.

Sam blushes and tangles his hands into the ball of fabric in his lap. He doesn’t meet his stare. “I want you to fuck me.”

Dean raises an eyebrow, but doesn’t come any closer. “There’s a bar down the street if you’re looking to get your rocks off,” he says evenly. “I’m sure you’d have no trouble grabbing yourself some interested tail if you wanted it. Why would you ask me?”

“Because I’ve never—” Sam stops himself short like he’s embarrassed. Like he’s never admitted the words out loud. His cheeks flush even redder as he shreds at his shirt. “I wanna know what it feels like,” he mumbles under his breath. “ _Sex_. You know how. Want you to show me.”

Dean skips over the easy Foreigner joke, mostly because his brother’s words happen to hit him so sweet. “You’re telling me you never got your dick wet?  _Ever?”_  He scoffs like he doesn’t believe it. Like maybe Sam’s just exaggerating. “C’mon, what about at Stanford?” he asks, finally bridging the distance between them. Dean had almost considered asking Sam to pretend that he’d never left for college at all, but the concept hit a little too close for comfort. Scraped right at the edges of his vulnerable underbelly. Sam just shakes his head shallowly, answering the question without a single word. “You’re seriously telling me there wasn’t anyone else?” Dean can’t help but prod again. “No hot co-eds?”

Sam’s eyes widen at the implications of the last question, knocked right out of character, and Dean feels his blood suddenly run cold. It’s too much. He went too far. It’s one thing to skim over actual events for the sake of foreplay, but another thing completely for Dean to ask Sam to renounce Jess out loud. Even if it _is_ just for some dumb game of make-believe. He’s already halfway through pulling back and stitching together a hasty apology when Sam shocks him stupid, snaking out a lightning-fast hand to firmly latch onto his collar. Dean goes as still as a statue. Doesn’t even dare to breathe as he waits for Sam to speak.

“No,” his brother eventually whispers. “No one else.”

Dean lets out a shaky exhale at the reprieve, Sam’s knuckles brushing against the base of his throat as he swallows. “Why?” His voice is so hoarse he barely recognizes it.

Sam finally glances up to meet his gaze, eyes open and honest. “I wanted you to be my first,” he says. And Sam is _not_ a good enough actor for that one to be anything but the truth. Dean can feel his ribcage go tumbling into his stomach at the quiet admission. Bones tinkling together as they splash into his guts like pieces of a broken xylophone. “The whole time. I always—” Sam cuts himself off with a jerk of his head, steering back into the safety of the game they’ve constructed. “So I saved myself for you.” He catches Dean’s eyes again. Steady.  _Honest_. “I wanted it to be you.”

He wonders if his brother can feel his pulse racing against the backs of his fingers. If Sam knows what he’s doing to him with just a few, deliberately-placed words. “…Because you want me to show you how?” Dean asks carefully.

Sam lets a faint smile curl at the corner of his mouth and shakes his head again. “Because I want it to be you.”

Dean half expects his brother to lunge at him. To come at him with years of repressed urges, all bottled up from his pretend life as a lonely virgin. It’s Sam’s go-to. Fast and ruthless and without mercy. But instead, Sam just waits there, his last words hanging in the space between them. Patient and submissive as he lets Dean set the pace. As he lets him wrap a tentative hand around the curve of his cheekbone. As he lets him lock their gazes one last time, just to make sure. As he lets him lean in and slowly, _reverently_ press their lips together. Keep them there. Like it’s their first kiss all over again. Gentler than their real first was though. And Dean is actually kissing back this time—participating, instead of frantically shoving Sam away out of fear. In fact, not just participating, but _leading_. Cradling his little brother’s perfect face in his hands and giving him everything he has, the way he always wanted to. Worshipping every bit of Sam he can reach. Like if he could go back in time a few years and actually do it right.

Sam lets a little, wounded noise escape, and Dean deepens the kiss, bringing a hand up to support his brother’s neck as he guides him back down to the bed. Then he yanks the t-shirt out of Sam’s hands and violently flings it across the room. Doesn’t even break away to breathe. He drops his lips to Sam’s neck, drags them across his collarbone, carefully tongues at each nipple until his brother is moaning and arching up underneath him. Until he’s trembling and needy and finally reaching out for him with the same fervor that Dean feels, his fingers latching themselves into the fabric of Dean’s shirt as he tries to pull him closer. 

“Please, Dean,” he breathes. “I want more. Everything.  _Please_.”

Dean can barely get Sam’s jeans undone fast enough. He rips his pants and boxer-briefs off in one go, and then manhandles his brother around until he’s on his hands and knees. Sam goes eagerly, ready and wanting, his hips already tilted up in expectation. And right there, front and center, sits his scar. Glaring at Dean like a judgmental beacon of failure.

“No, sorry,” he backtracks immediately, forcing Sam around until he’s blinking up at him again. “Not like—” He smoothes his hands down his brother’s sides, reaching down to gently spread his thighs. “Sorry," he whispers. "Here, like this.” Dean lowers his head for an apologetic kiss and settles himself between Sam’s legs. There. That’s more like their first time anyway.

Sam just nods like he _doesn’t_ know the exact reason for Dean’s hesitation, doing his best to pull them back into the scene. “Now what?” he asks shyly.

Dean gently nips at his fingers in silent thanks. “Now, little brother,” he replies with a muted smile. “Now I’m going to blow your freaking mind.”

He works Sam open slowly. Gentle and careful enough that he won’t feel even a hint of pain. And maybe Sam isn’t as tight as a real virgin, or as timid, but he thrashes and moans and trembles underneath Dean’s hands like he’s never experienced the heights of pleasure before. Like every single touch is the greatest thing he’s ever felt. Dean spends an hour bringing him off on just his fingers. A second time with his mouth. And then when Dean is finally holding his brother open with his own body, fusing them together with lazy thrusts and whispered words of praise, Sam keens so beautifully that he has to bury his face in his brother’s neck just to avoid revealing how much all of this is actually affecting him. But he’s sure Sam knows anyway. Sam always knows everything. Dean wonders if maybe his brother can read him solely from the tremors of his shoulders. From the way his arms grip tight and refuse to let go. From each hitched gasp of breath.

 _It’s only fair—_ Dean supposes.  _In the long run._  Because he can read Sam too.

“I liked that,” his brother whispers against his shoulder as they lay there afterwards, panting and exhausted. So quiet that he might not even have voiced it aloud.

But Dean doesn’t say a word. He’s not centered enough yet to make a joke about it and he’s not pussy enough to be honest. So he just rolls onto his side, facing away from Sam and hoping that his brother takes the gesture for what it’s supposed to be. Not condemnation or regret, just silence. Because he can’t deal with the rest of it right now. Thankfully, Sam seems to get it. He doesn’t push or nag, doesn’t force Dean into acting like an asshole by doing something stupid like trying to spoon him. He just lies back and lets it be, his left arm flush against Dean’s spine and holding steady. A warm point of connection between them. They’re okay for the moment. In fact, they’re actually pretty _good_.

Dean smiles. Maybe this whole roleplaying thing wasn’t such a terrible idea after all.

  

~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~

 

“So, you really have to tell the absolute truth?” Sam asks, believably awed. “Completely?”

Dean arches his back against the unforgiving wood of the library chair, just the slightest thrum of uncertainty edging at his nerves as he imagines every possible way this can go wrong. Sam’s got his arms braced on the table behind him, the bunker’s overhead lighting casting shadows across his temples as he cages him in, figuratively and literally.

“Yes,” he grits through his teeth, silently cursing his brother’s weirdo fucking libido. Why couldn’t he have just wanted Dean to throw on a French maid outfit or something? Or spurs and assless chaps. Y’know, like a normal person. “A witch got me or whatever,” Dean adds, and Sam pins him with a disappointed look for not playing along enthusiastically enough. He gives in with a short sigh, then tries his hand at sounding invested. “I’m not gonna lie— _can’t_ lie. ‘Cause of the magic and shit. Alright?”

Sam narrows his eyes and studies him for a suspicious handful of seconds, probably intent on testing the waters. “You cried the last time we watched Field of Dreams,” he says. “It wasn’t allergies.”

Dean shifts uncomfortably in his seat for a moment too long before finally letting out a frustrated growl. “I _teared_ up,” he corrects Sam. “Maybe. A little bit.” Then he glares at his brother and wonders if it’s too soon to cut and run without being teased for the rest of his life. “Which is a perfectly normal, _manly_ reaction to a baseball movie, thank you very much.”

Sam lets a broad grin spread across his face at the grudging admission, the _fucker_ , and drops fully back into character. He leans in close enough that Dean can feel his breath on the side of his cheek, trailing the tips of his fingers along the edge of his jaw. “How long have you wanted me?”

“Jesus Christ, Sam.”

“ _Truth spell_ ,” his brother reminds him obnoxiously, stretching down to nip at his earlobe. “You physically can’t lie.”

“I don’t know,” he says under his breath, already feeling his cheeks start to burn hot.

“That’s not an answer, Dean.”

Dean knows that if he really wanted to, he could safeword it. Or kick Sam’s ankles out from under him and shove his face into the floor until he tapped out. Which is probably more likely, considering. But Sam _did_ do the monumentally embarrassing virgin thing for him, and he didn’t even whine about it. At all. The least Dean can do in return is to see this through a little longer. Give the kid what he wants just long enough for him to rub one out. “Those goddamn Texas Chainsaw psychos,” he confesses reluctantly, his eyes boring holes into one of the cement pillars behind Sam so that he doesn’t have to look at his brother’s face. “The ones who hunted people.” He has to swallow around the sudden dryness in his throat before continuing. “You…you were missing for two days and I was scared out of my fucking gourd ‘cause I had no clue where you were.” And despite the tension still stretching at his nerves, Dean can’t quite stop his eyes from going soft at the memory. “Then, when I saw you again…”

His brother’s lips quirk into an amused smile as he thinks back over the events of that hunt. “Me in a cage?”

Dean gives him an almost imperceptible shake of his head. Sam wanted honest, he’s getting honest. “You _safe_.”

Sam’s eyes flick back up to meet his in surprise, wide and soulful. There’s a long pause as he tries to wrap his brain around the surprisingly mushy answer. “Really?” he asks quietly.

“Yeah,” Dean whispers back. “Really.”

And then Sam is instantly on him—wrenching him out of his chair only so that he can shove Dean back against the edge of the table and climb on top of him, grinding against his crotch through his jeans like he’s trying to power sand it raw. Dean groans, long and low, at the unexpected sensation, his own hands immediately snapping up to his brother’s sides so that he can lock him into place. A breathy laugh sneaks out as Sam latches onto his neck, and Dean tosses his head back for better access. Savoring each gorgeous little growl and whine being smothered against the base of his throat. Well that was way fucking easier than he thought it would be. And relatively painless, actually. Not even _close_ to the worst thing he’d ever put himself through in search of a no-strings lay. Sam’s hips start up into a perfect rhythm against his rising cock and Dean spreads his hands wide over his pert little ass in return, urging him on with every firm squeeze of his fingers. He’s just about to find out what his brother’s feelings are on the subject of quick fucks against library tables, when Sam pulls away with a sudden jerk.

“Wait, _wait_ ,” he breathes, shoving Dean flat on his back with one huge hand against his collarbone. “Hold on a second.”

“Oh, c’mon,” Dean groans impatiently, his hips still stuttering weakly as he tries to gather up his brain cells enough to focus. “What now?”

Although Sam’s still basically draped over most of him, he somehow manages to shift around until the good parts are barely touching at all and Dean’s about ready to _kill_ him. “No—wait. I wanna do more.” He pants out a heavy breath against Dean’s temple. “I’m not done yet.”

“ _Sam_.”

His brother completely ignores his pathetic whining, intent only on catching his gaze. “What happened to my copy of The Odyssey when I was fifteen?”

Dean lets out a frustrated sound as Sam continues his streak of being a world-class cocktease, but at least he can take solace in the fact that his brother has moved onto less-touchy topics. “Got ghoul juice all over it,” he answers honestly, straining up to mouth over the shoulder in front of him. “I secretly snagged it to read while I was on a hunt with Dad and it got fucking soaked in brain spatter.”

Sam lets out a beautifully broken moan (one that really shouldn’t exist anywhere _near_ the phrase “brain spatter”), but Dean is really finding it hard to care when his truthfulness merits him another brief jerk of his brother’s hips. He decides to push the envelope some more and traces his thumb over Sam’s lower lip until he obligingly sucks it into his mouth.

“Okay,” Sam mumbles around his finger, “remember the time you got hair all over your palms from jacking it? ‘Cause of that Antichrist kid? And then you swore on the Impala that you didn’t touch my razor—”

Dean lets his head fall back against the wood, interrupting his brother with a barked laugh. “’Course I used your fucking razor. You think my electric one woulda worked on something like that? I’d have ended up with freaky-gross stubble all over my hands.” He slips his thumb free so that he can cradle Sam’s face, then rolls their hips together again. “Plus, it was hilarious.”

“God, you’re such an asshole,” Sam gasps, but he goes boneless anyway, dropping his head into the crook of Dean’s neck. “Did Kimberly Wilson actually want to go to junior prom with me? Or did you just say that to make me feel better about us having to leave?”

“The pretty black girl with the braces?” He can feel Sam nod before he decides to drag his teeth over Dean’s tendon a second later, yanking his over shirt free and going to town on any bit of skin he can reach. “Yeah, she said it,” Dean hisses. “Came to the garage where I was working at the time and everything. Think she wanted me to give you a nudge.” He chuckles a little. “It was cute.” Sam grinds down _hard_ against his crotch, more gorgeous whimpers falling from his lips, and Dean clamps his hands around Sam’s narrow waist, to _keep_ him there this time.

 _God_ , he had no fucking clue that being honest about random little white lies would get his brother all hot and bothered like this. Who’d have thunk it? Hell, if it got him laid more often, he’d even be willing to tell Sam about the time he accidentally puked in his soccer cleats.

“What happened to my favorite pair of jeans?” Sam moans, struggling to match the rhythm Dean’s trying to set with his hands.

Dean slams his eyes shut, riding the wave of swelling arousal while trying to keep up with his brother’s questions as best he can. “Which jeans?”

“You know the ones. Dark wash, had a little hole in the right knee.” Sam groans at a particularly forceful thrust and claws his fingers into Dean’s shoulders. “They disappeared right after that vampire case in Utah.”

Sam collapses down onto his elbows, hair falling down around them, and Dean finally snags the correct memory. “Oh right, yeah,” he breathes, sweeping his hands up the broad spread of Sam’s upper back. “I used ‘em on the car.”

And then suddenly, all of the sexy grinding is gone in an instant. “ _What?”_ Sam asks tersely, looking extremely _not_ turned on anymore. “Are you serious?” Dean freezes in indecision until Sam eventually shoves away from him with a cut-off growl. “I _knew_ it! You said the machine at the Laundromat ate them!”

He blinks stupidly as he tries to catch up with the sudden mood whiplash, his brain still fuzzy from the receding promise of a sure thing. “Dude, who cares? You have plenty of other jeans.”

His brother looks at him like he’s just insulted Marie Curie—or some other one of his boring nerd heroes. “Well, those ones were my favorite!”

“They were _huge_ on you,” Dean says defensively as he props himself back up. “In fact, I practically did you a favor.” Sam’s eyes immediately go nuclear at that last statement, and Dean hastily scrambles for an explanation to salvage the moment. “Look,” he says reasonably, “it was completely unavoidable, okay? Baby needed a wash before the vamp blood could strip her paint job and they were the only expendable things in sight.”

“ _Expendable—?”_  Sam lets out a disbelieving scoff. “God, that’s just like you! You can’t steal my shit without asking, Dean! If you wanted a drying rag, you should have just used one of your crappy band t-shirts.” He slams Dean’s chair back into its place under the table with a violent screech of wood. “Like why not your old Survivor one?”

He can’t even pretend to hold back his derisive snort at the ridiculous suggestion. “Um, because fuck you?” Dean snipes. “Soaking my classic, ‘Eye of the Tiger’ concert shirt in vamp blood would be like throwing turpentine on the Mona Lisa.”

“The Mona Lisa,” Sam repeats dryly, fixing him with the most sarcastic look he’s ever seen. “Tell me, da Vinci. When’s the last time you actually wore it?”

Dean’s jaw clenches shut at the question and he glares at his brother, refusing to answer just on principle. Definitely _not_ because Sam actually has a point. “You know what?” he eventually says. “It doesn’t even matter. Because the epicness of my awesome t-shirt doesn’t change the fact that your jeans were _stupid_.” Sam lets out a huffy breath, then turns on his heel and stalks toward the exit without another word, his shoulders rigid with stubborn anger as he trots down the few steps into the war room. “And now they’re in Shammy Hell,” Dean calls out after his retreating back, “where they _belong!”_  Sam just silently flips him off as he rounds the corner, finally disappearing into one of the bunker’s hallways. “Yeah, you heard me!” Dean continues anyway, voice echoing off the now-empty archway. “In strips, Sam.  _Strips!”_

His brother doesn’t talk to him for another three days.

 

~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~

 

Sam graces him with a melodramatic roll of his eyes and ducks his head back under the spray of the shower. “No,” he says flatly. “Absolutely not. I am not dressing up like a _geisha_ for you.”

Dean crosses his arms over his chest and shifts a little until his ass isn’t quite so numb where it’s resting against the long row of sinks. “C’mon, man, it’s my turn. You have to do it.”

“Sorry, but no.” Sam slicks his hair away from his forehead, then flings his fingers back at him. “I’m vetoing the idea.”

“What?” Dean replies incredulously, dodging the sprinkling of warm, soapy water. His shirt gets hit anyway and he plucks at the damp fabric in irritation. “We don’t _have_ vetoes.”

“Of course we do,” Sam says snidely, smug as a slug in the rain. “I just used mine. Weren’t you paying attention?” He takes a few minutes to finish rinsing out his hair, then tosses Dean a look over his right shoulder. “You know, there are about a _thousand_ other rooms in this place,” he adds pointedly. “You don’t have to watch me shower.”

Dean scoffs and completely ignores the ridiculous statement. If his brother is so insistent on being a major buzz-kill, then the least he can do is let Dean enjoy the show. It’s not like the bunker gets Skinemax fifty feet underground.

  

~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~

 

Dean lets out a contented sigh as he relaxes back on his new memory-soft bed, Sam’s head on his chest as he casually runs his hands through his brother’s hair after a long day of doing absolutely nothing. “…Indian princess?” he suggests after a quiet moment.

Sam doesn’t even expend the energy to glare. “ _No_. _”_

  

~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~

  

“C’mon, it’s gotta be my turn by now.”

“Nope. You wasted your last turn on that stupid truth spell thing.”

Sam concedes the point with a barely-there roll of his eyes, then self-consciously glances at the rearview mirror again. “And why do _I_ have to be the one all dressed up?” he whines as he tugs at the leather clinging to his thighs.

“Because I don’t look half as good in fishnets,” Dean tosses back dryly as he puts the finishing touches on his brother’s messy eyeliner. And no, he ain’t gonna win any awards for neatness, but he’s seen chicks with the smudged look before, and it always seems to get the job done well enough for them. “By the way,” he says distractedly, “I can’t believe you’ll do _hooker_ , but you won’t do geisha.”

Sam snorts and awkwardly tries to hide his shoulders underneath the two-sizes-too-small wifebeater they’d managed to swipe from a thrift store clearance rack. “That’s because _hooker_ doesn’t put me in a dress.”

Dean eyes the tight, black fabric for a moment, but decides not to swing for the easy jab. “I dunno, Sammy. Think you might look good in the whole Julia Roberts get-up.” He lets a sleazy grin creep across his face. “What are your feelings on thigh-high boots?”

“I’m gonna put you in a goddamn Easter Bunny costume next time,” his brother threatens darkly.

“Whatever gets you hot, kiddo.” Dean lays a sharp smack to Sam’s leather-clad ass and boots him out the door. “Now get out of the car and stay away from any cops. I’ll pick you up at the next corner.” Sam shivers a bit in the cold night air before he starts to make his way up the sidewalk, looking for all the world like the sexiest streetwalker who specifically wants to murder him that Dean’s ever seen. “Oh—” Dean adds on second thought, half hanging out the window as he calls up the road, “and don’t forget to call me _‘stud’!”_

 

~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~

  

Despite the gnawing fear that Sam really _is_ planning on shoving him into some giant rabbit costume, just out of spite, their next escapade places them as a pair of high-profile lawyers working a case late at night. Dean doesn’t understand half of the legal jargon his brother is insistent on blabbing about before he’ll move on to the good stuff, but getting bent over someone else’s office desk with a tie stuffed into his mouth at two in the morning more than makes up for the earlier boredom.

They take another crack at cowboys once Dean is able to locate his hat from 1861, and although their subsequent romp gives new meaning to the term ‘riding’, he does have to admit that there’s a whole bunch of shit he _doesn’t_ miss about the Old West. Top of the list being the lack of hot showers—which, coincidentally enough, is what ends up leading them into round two. And who cares if cowboys didn’t have interior plumbing? Maybe he and Sam just happened to stumble upon a surprisingly warm waterfall while making their way across the prairie. Makes about as much sense as a phoenix in a duster, anyway.

A particularly disastrous attempt at recreating the bar scene from Raiders ends with a completely-plastered Sam informing him that, “…a cowboy hat ish defin-efitely _not_ the same thing ‘s a fedora, _Indy_ ,” and so many broken shot glasses that the bartender bans them both for life. Thankfully, they’d had the foresight not to use their brand-new local. Dean doesn’t think he’d ever be able to live it down if Donnie had been around to witness _any_ of that embarrassing spectacle.

Firefighters sends Sam into another one of his weird coughing fits.

Vampires just winds up putting Dean off.

And a valiant try at playing Doctor Sexy ends with three stitches and a bruised tailbone between them. Which Dean thinks is actually pretty faithful to the source material—but Sam refuses to look on the bright side of things because he’s a big, giant stick in the mud with a bruised tailbone.

 

~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~ 

 

“Okay, what about a delivery guy or a plumber or something? That’s classic, right?” Dean absent-mindedly gnaws at the end of a pen as he goes over his recently scribbled together list. They’ve already done all of the good ones, and then some, and now they seem to be stuck with the deep tracks. Not to mention that Sam keeps vetoing all his best ideas because he’s a _prude_ , and plumber sounds a lot better than most of the remaining pickings. Like babysitter. _Shudder_. “C’mon, Sammy,” Dean tosses across the room with an appropriately scuzzy leer. “You need someone to snake your drain?”

His brother just gives him a stink face from where he’s sprawled out on his back across his motel bed, browsing through one of the ancient, dusty tomes he’d grabbed from the bunker’s library. “How is that supposed to be sexy in any sense of the word?” he asks dryly. “I mean, really. Have you ever _seen_ a plumber?”

“Well, yeah…” Dean mumbles, wind successfully knocked out of his sails, “but maybe I’m a hot plumber.”

Sam just scoffs and goes back to his book. “No chance, Mario.”

“Fine,” he says, slightly disheartened as he glances back to the list. “I guess we could do a client/masseuse thing. Or, I don’t know, strippers maybe? I know it ain’t the most exciting thing in the world, but it’s better than—” Dean cuts himself off with a short intake of breath once he realizes that his brother is suddenly looming all up in his space, book nowhere to be found. He hadn’t even heard him _move_.

“Y’know, I think I’ve got a better idea,” Sam purrs, suggestively draping his arms around Dean’s shoulders before tugging them back toward the recently-vacated bed.

“Yeah?” Dean asks with an easy smile, letting himself be led.

“ _Yeah_.” Sam firmly shoves him back onto the mattress, and then crawls up after him, playfully grazing his fingers under the hem of Dean’s t-shirt. “But it’s pretty naughty,” he taunts lowly. “I’m talking _way_ forbidden here, man. Might be too much even for you.”

Dean practically salivates at Sam’s newfound indecency. “What are we talking here?” he asks enthusiastically. “Priests? S&M?” He raises an interested eyebrow. “Secret affair?”

“ _Better_ ,” Sam promises, brushing his lips over that one spot behind his ear. “Let’s pretend that I’m _me—_ ” Dean nods encouragingly, eyes gleaming as he waits for his brother to finish his thought. “…and that _you’re_ my older brother.”

 _…And_ the gleam is gone. 

“ _Sam_ ,” he says in his most unimpressed tone.

“Shh, hear me out,” Sam insists, stubbornly holding him down to the bed. “Let’s say that you’re the greatest hunter on the whole planet and you have a really badass car—”

“And an unbelievably handsome face.”

“… _But_ ,” he continues, expertly ignoring Dean’s interruption, “the only thing that matters to me is how I know you better than _anyone_ else in the world because we grew up together.” He pulls back just enough until he can catch Dean with one of his endearingly soft looks. All sweetness and rainbows. _Stupid puppy dog eyes._ “Hell, you practically raised me,” Sam goes on, gently tracing the edge of his thumb along Dean’s hairline. “And I spent my entire life looking up to you.” He drops his voice a shade. “ _Wanting_ you in every single way I shouldn’t. Because you were so perfect and so sexy and so good,” Sam ducks his head to punctuate each compliment with a brief kiss, and Dean can’t help but groan at the attention, “and you took care of me in every way you could. And even though you’re the one person I need more than anything,” he says earnestly, “you’re the only one I can never, _ever_ have.” Dean quickly reaches out for Sam’s hand on that one, tangling their fingers together before his brother can get all maudlin on him. “Because we can’t ever let anyone find out,” Sam picks up again. Then he tosses Dean a wry look. “ _And_ because you’re so scared of hurting me that you don’t wanna do anything that could screw me up or force me into this. Which is the _stupidest fucking idea_ you’ve ever had, by the way,” Sam adds with a sarcastic jab of his finger. He grins brightly once he’s made his point clear, and then dive-bombs directly for Dean’s mouth, using his tongue to lay claim to every available inch of real estate. “And then I sex you into submission with my amazing bedroom skills until you finally get it through your thick skull that this is the _one_ thing that we both need.” He gives Dean one last peck. Playful. “And then we live happily ever after.”

Dean always blinks for a little too long whenever he feels emotionally exposed. Like he’s subconsciously trying to hide his eyes. He can’t help it. It’s a stupid fucking tell that he _knows_ Sam knows about, but can’t seem to compensate for no matter how hard he tries. And he also knows that he’s doing it again, right this minute. “I think we still need to work a little on that last part,” he says quietly. Voice way too rough for his weak attempt at casual.

Sam lets a slow, unassuming smile crawl across his face. “I’ve got time,” he whispers back.

As his brother slinks tantalizingly down Dean’s torso to grapple with the fly of his jeans, he can’t help but think that maybe Dean Winchester’s got it pretty great already. And that maybe roleplaying is for suckers.

After all, no robber or cowboy or hot plumber gets to come home to a _Sam_.

 

 

 

 

**Author's Note:**

> Title taken from Cheap Trick's "Perfect Stranger"


End file.
